I didn't like 3.1 and the way you had to do things.
Windows 95 was somewhat better but still lacking.
Windows 98 was a major improvement, with 98SE making it a little better.
Windows XP dependability at least doubled that of 98. Ran like a dog with only 128mb memory. 1GB should have been minimum with 2gb the sweet spot.
Windows Vista was terrible. Trying to get it networked and share files with XP machines was a pain in the ass. Again, ran like a dog with less than 3-4 gb of ram even on Vista basic OS.
Windows 7 was much better, ran decently with 3gb of ram.
Windows 8 would have been much better if they would have incorporated the start menu in it, too hard to learn for older people. They didn't realize you could install classic shell or other programs and get the start menu back. They also should have made it default to show "computer", "control panel", "user files" shortcuts on the desktop.
The right click start menu for 8.1 wasn't any better.
I've used every OS since 3.1 and you can't consider windows 2000 as a consumer OS since it was more business related.
I've enjoyed XP and 7 the most though. And with classic shell, windows 10 is more like windows 7 anyway.